4-HO-DBT

4-HO-DBT
Identifiers
	IUPAC name N-Butyl-N-[2-(4-hydroxy-1H-indol-3-yl)ethyl]butan-1-amine;
CAS Number	63065-89-4 ;
ChemSpider	10579818 ;
UNII	R3EY4G4BLQ;
Chemical and physical data
Formula	C18H28N2O
Molar mass	288.435 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	74 to 75 °C (165 to 167 °F)
	SMILES CCCCN(CCCC)CCc2c[nH]c1cccc(O)c12;
	InChI InChI=1S/C18H28N2O/c1-3-5-11-20(12-6-4-2)13-10-15-14-19-16-8-7-9-17(21)18(15)16/h7-9,14,19,21H,3-6,10-13H2,1-2H3 ; Key:BDOJPNJIBDXWQQ-UHFFFAOYSA-N ;
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4-Hydroxy-N,N-dibutyltryptamine (4-HO-DBT) is a psychedelic drug belonging to the tryptamine family. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base. 4-HO-DBT was first made by the chemist Alexander Shulgin and reported in his book TiHKAL. Shulgin reported a dosage of 20 mg orally to be without effects. However this compound has subsequently been sold as a "research chemical" and anecdotal reports suggest that at higher doses 4-HO-DBT is indeed an active hallucinogen, although somewhat weaker than other similar tryptamine derivatives.

Several different isomers of this compound could be made (see DBT for a fuller discussion) but of these only the isobutyl isomer 4-HO-DIBT was synthesised by Shulgin (mp 152-154 °C) and was also found to be inactive at a 20 mg dose.

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